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Sailing Pro Ken Read on the Ultimate Regattas and the Industry’s Best-Kept Secret

The two-time Rolex Yachtsman of the Year winner shares his POV on all things sailing.

North Sails president Ken Read Illustration by Anje Jager

Sometimes, no matter how smart, connected, and well-resourced you are, you simply need an expert—and not just any expert, but the rarefied insider other specialists call when they need help. Luckily, Robb Report has a roster of such world-class pros on speed dial. We’re even rolling out a highly curated directory of heavy hitters across categories: the Masters of Luxury. 

This month, it’s Ken Read, president of North Sails and North Technology Group, considered the world’s finest sailmaker, with operations in 29 countries. Read’s unusually successful sailing history includes winning more than 60 world and national championships, skippering three America’s Cup teams, and leading multiple grueling round-the-world Volvo Ocean Races. He has also won the Rolex Yachtsman of the Year. Twice. 

Have a conundrum you’d like to see solved? Email [email protected] 

The Expert

Name: Ken Read
Occupation: President of North Sails and professional sailor
HQ: Newport, R.I.
Specialty: Mentoring and racing with new Maxi-yacht owners in regattas around the world

The Big Question

I’m a weekend sailor who wants to tick off a bucket-list item this summer by watching or even crewing in a world-class sailing event. I need advice on the best regattas out there and optimal locations. Any ideas? 

“One of the beauties of sailing is you can choose your adrenaline rush,” says Read, referring to how each event differs. “It’s symptomatic of the style of racing you’re doing.” It’s not just the sailing that makes a great regatta, he adds, but “the social events, parties, and local scene. There’s no way any sailor, or non-sailor, could not have fun.” So here’s his primer on the “insane variety” of race weeks: There’s the futuristic SailGP foilers streaking across San Francisco Bay, the classic 1930s wooden-yacht regatta in Monaco, and the world’s most technical (and expensive) Maxi yachts racing along Bomb Alley at the Maxi Yacht Rolex Cup Costa Smeralda in Sardinia. At the other end, the U.K.’s Cowes Week is “fun but mayhem,” says Read, where 1,000 sailboats are divided into 40 classes and the starting guns are antique cannons near Cowes Castle. At Les Voiles de Saint-Tropez, dozens of Maxi sailing yachts and hundreds of restored classic wooden vessels are docked stern-to in the historic port’s quays, while “thousands of visitors drool over these old boats,” packing the waterside cafés. Read has sailed Les Voiles many times, adding that it makes an exceptional vacation spot—the one thing all of these races share. “The goal of these regattas is to make you walk away going, ‘Holy shit, I wasn’t expecting that.’ ” 

Speed Round

I’m a seasoned sailor and want to crew a race. How? 

“Figure out a way to get through to an owner of a boat, maybe through connections at your local yacht club. Some companies are also entering old Volvo Ocean boats in these races with professional sailors in key positions, but everyone else on board is paying for what can be a bucket-list experience.” 

What race is sailing’s best-kept secret?

The North Sound Maxi Regatta in the B.V.I. just started in April. It has everything: unique backdrops and stunning waters, great sailing in T-shirts, and some of the world’s best Maxi boats. There’s off-the-water fun, dinners, and beach parties. One night, Bob Marley’s band, the Wailers, played on Richard Branson’s private island.” 

Best marina or shipyard for sailing-yacht refits?

“We like the STP shipyard in the center of Palma, Majorca. It’s a hidden gem on a beautiful island that has turned sailboat refits into a massive industry.” 

If you could sail only one regatta for the rest of your life, what would it be? 

“I do regattas all over the world, but I’d have to choose the New York Yacht Club’s Annual Regatta at my home base in Newport. There’s nothing like going out on a classic 12-meter vessel that’s completely souped-up and racing with old friends.” 

What should I know about the regatta scene right now? 

“We’re seeing a lot of new owners. They’re tutored by some of the world’s best sailors during the racing, and you get to race against them, too. How often can you get John McEnroe or Michael Schumacher on your team? Sailing lets you do that.” 

Either | Or

“If you’re a sailor, you’ve got to do a transatlantic once.”

“Monaco might be the nicest yacht club on the planet, but it’s not known for its great sailors. The New York Yacht Club is. There’s nothing like it when it comes to tradition.”

“Besides the company I work for, the America’s Cup is the best brand in sailing. It’s about controversies, challenges, billionaires, and crazy new boats. And the best sailors in the world.”

“I’m not a big fan of blue blazers. But the dry top is indispensable. It’s waterproof and breathable, and the neoprene neck and wrist seals are the only way to stay dry, even in the craziest conditions.”

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